Electrochemical cyclization of dimethyl aminomalonates

Synlett

Volumn , Issue 11, 2006, Pages 1753-1755

  Okimoto, Mitsuhiro ^a   Yoshida, Takashi ^a   Hoshi, Masayuki ^a   Hattori, Kazuyuki ^a   Komata, Masashi ^a   Numata, Kaori ^a   Tomozawa, Kenta ^a  

^a KITAMI INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Cyclizations; Dimethyl ester; Electrochemical oxidations; Electron transfer; Heterocycles

Indexed keywords

DICARBOXYLIC ACID; DIMETHYL 1 BUTYL 2 PROPYLPYRROLIDINE 3,3 DICARBOXYLATE; DIMETHYL 1 PROPYL 2 ETHYLPYRROLIDINE 3,3 DICARBOXYLATE; DIMETHYL 7 METHYLHEXAHYDROINDOLIZINE 1,1 DICARBOXYLATE; DIMETHYL AMINOMALONATE DERIVATIVE; DIMETHYL HEXAHYDROINDOLIZINE 1,1 DICARBOXYLATE; DIMETHYL HEXAHYDROINDOLIZINE 8,8 DICARBOXYLATE; DIMETHYL HEXAHYDROQUINOLIZINE 1,1 DICARBOXYLATE; DIMETHYL TETRAHYDROPYRROLIZINE 1,1 DICARBOXYLATE; ELECTROLYTE; MALONIC ACID; METHANOL; SODIUM CYANIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; ELECTRON TRANSPORT; OXIDATION; ROOM TEMPERATURE;

EID: 33746277805     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-944205     Document Type: Article

References (28)

1. For example see: (a) Weinberg, N. L. Technique of Electroorganic Synthesis; Wiley-Interscience: New York, 1975.
2. (b) Torii, S. Electroorganic Synthesis; Kodansha: Tokyo, 1985.
3. (c) Okimoto, M.; Takahashi, Y. Curr. Org. Synth. 2004, 1, 233.
4. (d) Shono, T. Tetrahedron 1984, 40, 811.
5. (a) Okimoto, M.; Chiba, T. J. Org. Chem. 1988, 53, 218.
6. (b) Chiba, T.; Okimoto, M. Chem. Lett. 1993, 521.
7. (c) Okimoto, M.; Chiba, T. J. Org. Chem. 1993, 58, 6194.
8. (d) Okimoto, M.; Takahashi, Y. Synthesis 2002, 2215.
9. (e) Okimoto, M.; Takahashi, Y.; Nagata, Y.; Sasaki, G.; Numata, K. Synthesis 2005, 705.
10. (a) Chiba, T.; Okimoto, M.; Nagai, H.; Takata, Y. J. Org. Chem. 1983, 48, 2969.
11. (b) Okimoto, M.; Chiba, T. J. Org. Chem. 1990, 55, 1070.
12. (c) Chiba, T.; Okimoto, M. J. Org. Chem. 1992, 57, 1375.
13. (d) Okimoto, M.; Itoh, T.; Chiba, T. J. Org. Chem. 1996, 61, 4835.
14. (e) Okimoto, M.; Takahashi, Y. Bull. Chem. Soc. Jpn. 2002, 75, 2059.
15. (f) Okimoto, M.; Takahashi, Y.; Kakuchi, T. Synthesis 2003, 2057.
16. (g) Okimoto, M.; Numata, K.; Tomozawa, K.; Shigemoto, T.; Hoshi, M.; Takahashi, Y. Aust. J. Chem. 2005, 58, 560.
17. (a) Hart, N. K.; Johns, S. R.; Lamberton, J. A. Aust. J. Chem. 1972, 25, 817.
18. (b) Leonard, N. J. The Alkaloids, Vol. 6; Manske, R. H. F., Ed.; Academic Press: New York, 1960, 35.
19. (c) Glasby, J. S. Encyclopedia of the Alkaloids; Plenum Press: New York and London, 1975.
20. (a) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinred, S. M. J. Am. Chem. Soc. 1981, 103, 6387.
21. (b) Howard, A. S.; Gerrans, G. C.; Meerholz, C. A. Tetrahedron Lett. 1980, 21, 1373.
22. (c) Macdonald, T. L.; Narayanan, B. J. Org. Chem. 1983, 48, 1129.
23. (d) Stevens, R. V. The Total Synthesis of Natural Products, Vol. 3; ApSimon, J., Ed.; Wiley-Interscience: New York, 1977, 439.
24. (e) Robins, D. J. Advances in Heterocyclic Chemistry, Vol. 24; Katritzky, A. R.; Boulton, A. J., Eds.; Academic Press: New York, 1979, 247.
25. (f) Blum, Z.; Ekstrom, M.; Wistrand, L.-G. Acta Chem. Scand. B. 1984, 38, 297.
26. Csendes, I. G.; Lee, Y. Y.; Padgett, H. C.; Rapoport, H. J. Org. Chem. 1979, 44, 4173.
27. Shono, T.; Matsumura, Y.; Uchida, K.; Tsubata, K.; Makino, A. J. Org. Chem. 1984, 49, 300.
28. Chiba, T.; Takata, Y. J. Org. Chem. 1977, 42, 2973.